Waylon Jennings Auction Offers Rare Treasures

The late Waylon Jennings was one of a kind. And let’s admit it. Any of us would be thrilled to own one of the Country Music Hall of Famer’s personal belongings.

If you’re willing to pay what we can assume will be a hefty price, you can make that dream come true this fall.

Jennings’ wife Jessi Colter is at the helm of an auction of some of his most prized possessions to benefit the Phoenix Children’s Hospital. Many of the 2,000-plus items up for grabs are nothing short of mind-blowing. The singer counted Buddy Holly, Willie Nelson, Kris Kristofferson and Johnny Cash among his famous friends, and the items up for auction underscore the closeness of those relationships.

At the center of this massive collection is a British-made Ariel Cyclone motorcycle Holly bought in 1958. Jennings gave up his seat to Holly on a private plane that crashed following a 1959 concert. Holly, Richie Valens and the Big Bopper were all killed in the accident in Iowa. Jennings later acquired the motorcycle.

Other items confirmed in the auction are the original signed contract signaling the beginning of the Highwaymen, the supergroup of Jennings, Nelson, Cash and Kristofferson, along with Nelson’s hair braids which — so the story goes — Nelson himself cut off in 1983 to support Jennings’ road to sobriety journey. There’s also Hank Williams Sr.‘s cowboy boots created by Nudie Cohn, the famous tailor to the stars, and a handwritten letter to Jennings from John Lennon.

Just reading the descriptions of these items makes you wonder what it would’ve been like to be present in those moments, doesn’t it? I probably would have screamed the moment Nelson took scissors to his braids. Have mercy!

Photos, stage wear and awards will also be up for grabs when the auction takes place Oct. 5 at the Musical Instrument Museum in Phoenix. The auction is being organized by Guernsey’s
, a New York city-based auction house.